


Not How It Was Supposed to Go

by AnimeLoveLover123



Series: Crossdressing [3]
Category: Deadpool - All Media Types, Spider-Man - All Media Types
Genre: M/M, Shy Peter, Spideypool - Freeform, What am I doing?, cross dressing, cross dressing Peter
Language: English
Status: Completed
Published: 2016-05-28
Updated: 2016-05-28
Packaged: 2018-07-10 15:39:58
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,334
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6991684
Author URL: https://archiveofourown.org/users/AnimeLoveLover123/pseuds/AnimeLoveLover123
Summary: <blockquote class="userstuff">
              <p>“This is a horrible idea.” Spider-man thought as he sat in the closed paper recycling bin of Deadpool’s apartment complex waring a cheep, sexualized spider-woman Halloween costume. “A horrible, horrible idea.” </p><p>P.S. I suggest you click the link in the notes to see the outfit Spider-man is waring first.</p>
            </blockquote>





	Not How It Was Supposed to Go

**Author's Note:**

> Link to outfit -> http://animelovelover123.tumblr.com/post/145028141430/hay-there-this-is-just-a-reference-for-one-of-me

Spider-Man felt like an idiot sitting atop what he hoped was only cardboard and loose leaf paper as he couldn't see with the lid to the bin closed over his head. The person he had thankfully heard coming was long gone so there really was no reason for him to hide anymore, but that didn't stop him from staying put so he could assess the situation.

Thanks to his stupid big mouth, he made the promise to get Deadpool back for what he had done without actually thinking through the revenge plan first. And of course his stupid pride would not allow him to just come up front to the mercenary. No he had to do something ridiculous like put on a cheap Halloween costume that the Human Torch had bought him for his birthday as a joke. 

Why was he even doing this? He had looked himself over in the mirror before leaving his apartment and could tell with just one glance that he wasn't pulling female clothing off half as well as the mercenary. Which then began yet another erection which lead to a panic attack and ended with a valiant assurance that he was totally straight as he left his apartment in a skimpy outfit with the goal of getting another guy hard. And yes, Spidey realized how stupid and nonsensical that sounded but never the less he was determined to stick to his guns, even if every time he caught a glimpse of himself he doubted his plan more and more.

He was supposed to excite the mercenary but all he saw was an idiot. He looked more ridiculous considering he wore such a revealing outfit but still maintained his full head covering mask. But if he was going to do this he was at least going to save Peter Parker's shame from getting involved. 

The rest of the outfit didn't leave much to the imagination however.

He didn't know if he should be thankful that the waist of the outfit wasn't constricting his already queasy stomach or mortified with the fact that there wasn’t a middle to the outfit at all. A long spider shaped peace of cloth was the only thing connecting the strip covering little of his chest and the skirt. He decided to be mortified.

The straps hung loosely off his shoulder restricting his arm movement, not that he attempted to swing with his webs. The moment Spidey felt the first rush of wind ruffle the cheap fabric of the skirt ever so slightly he realize that taking the quick road to Deadpool's house was not an option.

Sneaking his ways through the shadows wasn't exactly the best plan either. All it did was leave him time to regret his decision and question whether he should turn back. But as he finally felt brave enough to peek out from the recycling bin lid and look up at the apartment complex before him he realized that if he had gone this far it would be a total waste to go home now.

Deadpool would face the embarrassment of getting aroused when he really shouldn't even if it killed Spider-Man, which it looked like it was going to.

At least Spider-Man was being kind enough to let the mercenary be embarrassed within the walls of his own home unlike the very public display given to Spidey. Or maybe that was just his excuse to avoid even more embarrassment. Ether way, the vigilante crept out of his hiding place and made a mad dash for the mercenary's apartment window, thankful that the lock still seemed to be broken, giving easy accesses to the living room.

“It's just me!” Spider-man announced, not wanting to set off the mercenaries fighter instincts. As he found his footing, glad that he could find a relatively clean part of the floor to stand on, he could hear the creaking of a bed then a pair of feet hitting the ground and making a dash to the living room.

“Spidey! I've been looking for y-” Deadpool froze in the doorway, jaw dropping as he placed a hand on the wall, worried he might faint.

Spider-man, THEE Spider-man was wearing a dress, and damn did he look fine, in Deadpools opinion.

The vigilante kept his eyes on the floor, away from the olders stare, arms wrapping around his torso in a futile attempt at covering himself.

“Something wrong?”Spider-man finally asked, glad that his mask was covering his scarlet cheeks. Deadpools eyes snapped up to meet Spideys.

“Legs? I mean what? No, nothings wrong.” The mercenary stammered, not missing the way the youngers legs crossed at his words. “Uuuuuu...” Deadpool droned, eye's falling back down to those slim, smooth, yet strong legs he wouldn't mind being stuck between. 

“You said you've been looking for me?” The web-slinger reminded awkwardly as he tugged the end of the dress down a tad, suddenly feeling shame in himself and regret for all the women he had stared at since high school.

“What? I mean yes, I have.” Deadpool stated eye's lifting up again, momentarily getting caught on the youngers six pack and the slightly visible line of hair trying to direct him back down. “I wanted to apologize for last time. I wasn’t going to laugh at you, I was trying to hold down a boner.” 

Spidey knew he should have but couldn’t help the way his already thudding heart beat sped up. He had figured that was what the mercenary was actually doing later that night after he had calmed down. It left a pleasant feeling in his lower gut however to have the older say it.

While pushing down the slight pride he told himself he shouldn't be feeling, Spider-man opened his mouth, about to say something, before realizing that Deadpool had been speaking while he was lost in thought.

“but that's not really helpful because I can't fight down the massive erection I have right now so-”

“What!?” Spider-man cut in, causing Deadpool to jump back slightly at the sudden shout.

 

“What?” The mercenary asked back.

“You can't just say that.”

“Say what?”

“That you... you....” The younger stammered, embarrassment and confusion preventing him from using a crude word.

“Find you ridiculously hot.” The mercenary guessed, feeling a bubble of giddiness at the way Spidey shied away from the compliment.

“No, not that.”

“That I have a raging boner?”

“Yes, that. You can't just say that.”

“Why not? You can totally see it if you just look down a bit.” The mercenary said, making a hand gesture to his lower region to which the web slinger did not take the bate.

“Well sorry, but I haven’t been looking at your crouch.” Spider-man said, trying not to but failing to miss, out of his peripheral vision that yes, Deadpool was very excited.

“Why not? Wasn’t the whole point of dressing up all sexy to give me a stiffy? Or is this a come on because if so-”

“The point wasn’t to give you a boner.” Spider-man jumped in because part of him was still holding on to his pride and the idea that he was straight as a board, even if the rest of him knew something was up. “It was to embarrass you like you embarrassed me. Though I should have known it would be less embarrassing in your home then having all of New York see.” He mumbled to himself but Deadpool got it.

“Well if that's what you want.” The mercenary said with a shrug. He knew he had gone a bit far last time and he was willing to take the consequences if it meant getting closer to those lean legs.

“What are you doing.” Spidey asked, a wary eye following the older as he approached the open window the vigilante had entered from. Deadpool stuck his head out of the window, cupped his hands around his mouth, and shouted as loud as he could.

“HEY NEW YORK! I, DEADPOOL, HAVE A MASSIVE BONER FOR SPIDER-MA-” A line of webbing grabbed the mercenaries lower back and was pulled with enough strength and speed to cause him to hit the opposite wall.

“What the hell do you think your doing!” Spidey screamed as the older stumbled his way to his feet. “Do you have any shame?”

“Isn’t this what you wanted?” The mercenary asked, honestly confused.

“No... I...” Those two words came out broken and quiet, causing the mercenaries chest to collaps in on itself. Spider-man turned his back to the older and burried his face in the curtains, hands clutching at the worn and stained fabric.

“Spidey...” Deadpool called quietly, hand raised in the youngers direction.

“Don't talk to me.” The vigilante spat, hoping that the anger in his tone disguise the fact that he was on the brink of tears. It didn't.

What had he been thinking? How was doing this in any way, shape, or form, a good idea? Why couldn't the earth just open him up and consume him?

As the younger cursed to himself inwardly, Deadpool watched as Spider-man, the everyday hero he idolized, practically curl himself up in the corner of his living room.

“Why do I always fuck things up?” The merc with the stupid mouth asked himself.

The vigilante could hear the older approaching, leading to his whole body stiffening. Instinctively Spidey reached behind himself and held the skirt down, not putting it past the mercenary to try flipping in up. To be fair though, Deadpool had considered it.

Instead a thin blanket was draped over Spider-mans bare shoulders.

“I have some spare clothing in my bedroom. You can change in to anything that fits and make our way home in those.” Deadpool offered with a light smile, though it was hidden by the mask.

Spider-man slowly turned to face the older, quickly grabbing the edge of the blanket and wrapping it around himself. The web-slinger just watched the mercenary for a long moment, mind a little scrambled by the offer and apologetic tone.

“Thanks.” He was finally able to say before shuffling past the mercenary to the bedroom. With his head hung low and mouth held shut, Spider-man went about searching the drawers for something to cover himself, all the while unable to wipe a smile from his face. He was still embarrassed and a bit ashamed but his chest fluttered a bit at the olders kindness.

He rummaged through the drawers, easily finding a t-shirt to throw over his head. Pants where seeming to be a bit of an issue as any he could find where a size or two to big to hold themselves up on his hips. He tried looking for a belt but all of them have various pouches and weaponry attached to them.

Maybe he could find something in the closet.

Wade on the other hand sat cross-legged on his couch staring down at the bulge in his pants that just wouldn't go down and it was all Spidey's fault.

When he tried to push down the tantalizing image of what he could have seen by flipping Spidey's skirt up, he ended up unearthing the realization that Spider-man was changing in the mercenaries bedroom. That god blessed figure was getting naked in his room and then putting on some of his clothing like they where boyfriends and-

Deadpool let out a squeal at the thought, flopping down on his stomach across the couch.

He tried to calm his beautiful fantasies and take a few deep breathes. He was doing so well, being all chivalrous but how could any living person not want to jump Spidey?

Slowly Deadpool raised his head, finding it a bit hard to breath through his couch, when he noticed that the bedroom door was open a bit. He turned his head in confusion as he stood from the couch to carefully approach the slightly ajar door.

This... this was totally an invitation right? Spider-man was luring him into his spider web and would eat him, the sexy way hopefully.

Silently the mercenary sneaked his way to the bedroom and peeked in. His eyes where instantly drawn to Spidey in one of the mercenaries shirts and dear god he was gorgeous. Those slender, smooth legs and that tiny bit of tush peeking out from under one of the mercenaries rarely used t-shirts and the youngers tighty whiteys. What an adorable dork.

Deadpool was so distracted with idolizing the hero that he didn't notice that Spider-man was looking through his special closet until one of the outfits where pulled out.

“Hey!” The younger nearly jumped out of his skin at the shout, dropping the dress he held as if it burnt him. “What are you doing with my new cloths?” The mercenary asked rather calmly as he swung the door open and walked in.

“N-new cloths?” Was all Peter could stammer out, half knowing that acting dumb wasn’t going to help at all.

“I bought them all just for you.” The mercenary said, a sly grin coming to his lips as Spider-man grabbed the front edge of his shirt and pulled it down a bit lower.

“Subtle Parker.” The vigilante thought to himself as he bit his bottom lip in frustration. 

“Want me to wear them for you?” Spider-mans whole body stiffened, eye's screwing shut in a futile attempt to block out the mental images while his fist pressed lightly against his slowly growing erection in hopes of keeping it down. “A little fashion show maybe?” Deadpool said, leaning into the youngers space who seemed to almost cower in response.

“I'm straight.” The younger stated plainly, not sure whether he was telling the mercenary or himself.

“Riiiight.” Deadpool said with a roll of his eyes. The moment then fell into an awkward silence, the older questioning whether he should take his leave or jump the spider.

“This one.” Spider-man finally said, reaching out a hand and tugging shyly at one of the various outfits. “Start with this one.”

**Author's Note:**

> Now who wants to write Wade's fashion show and the inevitable smexing? Because I won't, but I'm not against seeing what someone else could come up with.
> 
> Link to outfit -> http://animelovelover123.tumblr.com/post/145028141430/hay-there-this-is-just-a-reference-for-one-of-me
> 
> Oh my gosh, It's finally done! I know this last part took longer then it should have, sorry. ^^; I had a hard time figuring out how to tie everything up in the end. Trying to make it funny but also have a bit of heart in it. Show that Deadpool actually cared about Spidey, at least a little, and that, despite telling himself over and over, Spider-man kind of accepting that he wasn’t the straightest nail in the shed.
> 
> Hope it was worth the wait.
> 
> Update: Oh my gosh, someone drew a pic for this story!  
> http://void-bee.tumblr.com/post/145284792186/a-little-doodle-of-peter-in-a-spideylady-dress
> 
> I don't own Deadpool or Spider-man.


End file.
